Vacation rentals in Maidstone

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Top-rated vacation rentals in Maidstone

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
The entrance to The Annex features a well-defined porch with a welcoming door. Flower pots with red blooms sit on either side of the entrance, while a gravel pathway leads up to the front, framed by greenery from nearby plants.
Home in Leeds
4.99 out of 5 average rating, 187 reviews

Self-contained luxury annex

The Annex is a completely private part of our house for guests exclusive use, located in the historical Kentish village of Leeds, within walking distance to stunning Leeds Castle. Located 5 minutes from J8 M20. Ideal for Leeds Castle. The Kent show ground. 35 mins drive to Eurotunnel & 50 mins to Dover ferry port. 1 hour to London via train. The Annex has it's own private entrance, rear private patio area, sitting room/ fully equipped kitchenette, downstairs shower room/ large upstairs bedroom.

Top guest favorite
The exterior of the annex is showcased, featuring vertical wooden slats and a glass-paneled door. A small window is visible, allowing natural light into the space. The entrance is set on a paved path, surrounded by greenery and a water storage tank nearby.
Guesthouse in Sittingbourne
4.93 out of 5 average rating, 259 reviews

Self-contained annex, with off-road parking.

Self-contained annex in Sittingbourne, perfect if you are visiting the area for work or leisure. Everything you need for a comfortable stay in your own completely private place, with driveway parking and fast WiFi. The accommodation comprises a bedroom /lounge /working room, kitchen and bathroom. The annex, especially the bedroom, is very quiet and peaceful. Located conveniently for the motorway and also easy access to the town centre, train station, shops, takeaways, restaurants and pubs.

Guest favorite
The exterior of a modern annex is depicted, featuring a sloped roof, large windows, and a wooden deck. Surrounding greenery includes well-maintained grass and flowering plants, contributing to a calming outdoor environment. The scene is set against a backdrop of cloudy skies.
Guesthouse in Detling
4.87 out of 5 average rating, 190 reviews

Adorable 1 bed guesthouse with patio

Sit back & relax in this calm, cosy space. Set within the grounds of our gated family home in Detling located on the slope of the North Downs, 4 miles north east of Maidstone, & on the Pilgrims' Way. Whether you want a relaxing get away or want to explore many of the wonderful walks and bike trails the north downs have to offer you can be sure to find a warm and cosy place to stay at the end of the day. We have a very friendly dog who will be on hand to greet you along with 2 young children

Top guest favorite
A quaint entrance is framed by a variety of colorful flowers, including pink and purple blooms, cascading from hanging baskets and garden beds. The rustic wooden door is set against a whitewashed wall, complementing the charming brick pathway leading up to it.
Place to stay in Addington
4.98 out of 5 average rating, 228 reviews

Petite Gite in an idyllic cottage garden.

Come and make yourself at home in this unique hand crafted miniature gite. Tucked away in the garden of a Tudor cottage, situated on the Addington village green just yards from the Angel Inn. Cottage style Kitchenette with miniature Belfast sink and cupboards. Small double raised bed with storage and dining table underneath. Fully centrally heated for those cosy winter/autumnal days. Rose Cottage, as we call it, has been painstakingly restored to create a delightful, light and cosy space.

Superhost
A modern kitchen area features sleek dark cabinetry and stainless steel appliances, including an oven and microwave. Two pendant lights hang above a wooden bar with seating for two. A light gray sofa is positioned nearby, complemented by an orange decorative pillow.
Apartment in Kent
4.88 out of 5 average rating, 131 reviews

The Bohemian Basement

The Bohemian Basement is a unique stylish one bed apartment with its own private garden in the heart of Maidstone. The apartment is 1 of 3 within a newly converted Victorian property just minutes walk from the town centres shops, restaurants and bars. Perfectly equipped with everything you’ll need while visiting Maidstone and with the added bonus of having a wonderful private outdoor garden space, makes this a fantastic Airbnb. There is free on street permit parking which we supply.

Top guest favorite
A charming outdoor seating area features white metal chairs and a small table set on wooden decking. Potted plants flank the seating arrangement, and a brick wall provides a backdrop. The space is bordered by lush greenery, offering a serene environment.
Guesthouse in Tonbridge
4.97 out of 5 average rating, 311 reviews

Weald Lodge: self-contained annexe with parking

This stylish place to stay is perfect for couples looking for a country get away with walks across the fields. Driving distance to local amenities, pubs/restaurants & attractions. Weald Lodge is a separate annexe in the gardens of Wealdview Farmhouse (TN12 6SP) PLEASE NOTE, despite being in the category of farm, we are not a farm and do not have far machinery. The fields around us have grazing sheep Due to the open beams on the mezzanine level, we don't encourage infants or children

Guest favorite
The exterior of the annex is presented, featuring a white picket fence and a gravel area. A vintage lamppost stands near the entrance, complemented by two outdoor chairs positioned on the patio. The structure showcases a pitched roof, rustic siding, and several windows, providing ample natural light.
Cottage in Boughton Monchelsea
4.9 out of 5 average rating, 790 reviews

The Oast Cottage: Private Annex with own entrance.

We are pleased to offer our refurbished annex with double bedroom, private bathroom, own front door and a private field for dogs. Oast Cottage is a converted stables attached to the main Oast House. The Oast is set in a conservation area of Boughton Monchelsea which consists of converted farm buildings, listed houses and a 16th Century pub (directly opposite). The area boasts many places to visit (including Leeds Castle), countryside walks, as well as numerous pubs.

Top guest favorite
An open plan living area features a circular wooden table surrounded by teal chairs and a cozy seating arrangement with a leather sofa and armchair. A television is positioned beside a decorative fireplace, while natural light filters in through windows overlooking lush greenery.
Guest suite in Wateringbury
4.99 out of 5 average rating, 263 reviews

Peaceful apt, views, garden, WiFi & sunsets

Relax or work in this stylish apartment with private courtyard garden and vintage summerhouse * First floor apartment with free parking * Country views * Wi-Fi * Self check in * 6ft super king bed * Heating * Smart TV * Plus a summerhouse * Under 1 hour train from London * Local pub/food 10 minute walk * Close to country walks * River Medway 1 mile for boating/walks * Not suitable for pets or children * Please note EV charging is NOT permitted on the property*

Top guest favorite
A well-lit bedroom features a spacious bed with a combination of white and orange bedding. Two framed artworks are mounted on the wall above the headboard. Natural light streams in from a large window, which offers a view of the surrounding area.
Bungalow in Allington
4.97 out of 5 average rating, 118 reviews

Maidstone Bungalow sleeps 5 with parking

This stylish bungalow boasts with unique features and has everything you need for a comfortable stay. Open plan living space is airy and bright and compliments fully equipped modern kitchen. This 2 bed fully refurbished single level home sleeps up to 5 people and it can provide both king size and single beds. The bungalow is located in a prominent position in Allington, Maidstone, and it offers off road parking for multiple cars and a private garden.

Guest favorite
Double doors open to a private garden highlighting a well-maintained lawn and patio area. A circular table with ornate chairs is positioned centrally, and a barbecue station is visible in the background. The scene is illuminated by natural sunlight.
Home in Kent
4.92 out of 5 average rating, 289 reviews

Hermitage Cottage cosy 1-4 person accommodation.

Hermitage Cottage offers annexe accommodation. Bathed in sunshine in private garden setting. We are a commuters dream with Barming railway station at the door. London Victoria 57 minutes and Maidstone East just three minutes by rail. Fully fenced with garaging for one vehicle., entry by automatic gates. Finished to a very high standard with under floor heating and feature fire place. Your every comfort is assured. Welcome pack included.

Top guest favorite
A spacious living area showcases wooden beams and an open layout. A comfortable sofa faces a wood-burning stove, with a flat-screen TV nearby. The dining table is surrounded by woven chairs, and large windows provide natural light while offering views of the entrance and surrounding nature.
Cottage in Marden
4.99 out of 5 average rating, 571 reviews

The Lodge

**Opted in to Airbnb's enhanced cleaning protocol** Cosy barn-style accommodation nestled in the heart of the Kent countryside. Located close to National Trust sites and country walks. The Lodge is the perfect country getaway and romantic retreat. Please note this is strictly a NO SMOKING property inside the Lodge, the garden and surrounding field. The property is also NOT SUITABLE for infants, children or pets. Two adults only.

Guest favorite
The exterior of a single-story lodge is featured, showcasing a dark wood facade and a sloped roof. A manicured lawn surrounds the structure, with a pathway leading to the entrance. Nearby, trees and another building are visible, creating a serene, rural atmosphere.
Cabin in Medway
4.87 out of 5 average rating, 340 reviews

Peaceful 2 bedroom country lodge

A self contained space, with beautiful garden space and lake access nearby. Surrounded by wildlife, you'll hear birds, horses and maybe even the local alpacas! Comfortable sofas and beds will help you rest, and a complete kitchen including washer/dryer means you can lock yourself away or get out and about We are rural and in a valley - mobile signal is low and the internet’s not fast.

Popular amenities for Maidstone vacation rentals

When is the best time to visit Maidstone?

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Frequently Asked Questions

  • What are the most popular amenities for Apartment Rentals in Maidstone?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 80 homes with a kitchen, over 40 homes with free parking, over 80 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Where should I stay in Maidstone?

    Make yourself at home in Maidstone by choosing from our most frequently booked neighborhoods. We have over 280 vacation rentals in Penenden Heath, over 120 vacation rentals in East Farleigh, and over 60 vacation rentals in Detling.

  • Do condo rentals in Maidstone have a kitchen?

    Absolutely! We offer over 20 condo rentals with a kitchen in Maidstone. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Maidstone have free parking?

    Absolutely! We offer over 40 apartment rentals with free parking in Maidstone. Enjoy a tailored experience with all the comforts you desire.

  • Are there apartment rentals with a dedicated workspace in Maidstone?

    Yes! Work meets play with ease at over 40 apartment rentals in Maidstone featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly house rentals in Maidstone?

    Four-legged friends are welcome in Maidstone. Choose from more than 30 house rentals for guests traveling with pets.

  • Are there family-friendly house rentals in Maidstone?

    Maidstone has more than 60 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in serviced apartment rentals in Maidstone?

    Experience the best of Maidstone with our serviced apartment rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about vacation rentals in Maidstone

  • Total vacation rentals

    Explore 290 vacation rentals in Maidstone

  • Nightly prices starting at

    Maidstone vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 4,150 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    270 of Maidstone vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Maidstone rentals

  • 4.6 Average rating

    Maidstone stays receive an average rating of 4.6 out of 5 from guests

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